| Year | Host | Winner | Club Represented |
|---|---|---|---|
| 1972 | Rick Bowe | Severn Sailing Association | |
| 1973 | Rick Bowe | Severn Sailing Association | |
| 1974 | Tred Avon Yacht Club | Vance Strausburg | Tred Avon Yacht Club |
| 1975 | |||
| 1976 | Kin Yellot | Severn Sailing Association | |
| 1977 | |||
| 1978 | |||
| 1979 | |||
| 1980 | |||
| 1981 | Fishing Bay Yacht Club | Jonathan Phillips | Severn Sailing Association |
| 1982 | Fishing Bay Yacht Club | James Jacob | Potomac River Sailing Association |
| 1983 | Fishing Bay Yacht Club | ||
| 1984 | Fishing Bay Yacht Club | Jonathan Phillips | Severn Sailing Association |
| 1985 | Fishing Bay Yacht Club | Jonathan Phillips | Severn Sailing Association |
| 1986 | Fishing Bay Yacht Club | Mike Waters | Severn Sailing Association |
| 1987 | Fishing Bay Yacht Club | Max Skelley | Havre de Grace Yacht Club |
| 1988 | Fishing Bay Yacht Club | Nicky Adamson | |
| 1989 | Old Dominion University | ||
| 1990 | |||
| 1991 | Havre de Grace Yacht Club | Max Skelley | Havre de Grace Yacht Club |
| 1992 | Havre de Grace Yacht Club | Rusty Deane | |
| 1993 | Tred Avon Yacht Club | Eric Naranjo | |
| 1994 | Havre de Grace Yacht Club | Rusty Deane | |
| 1995 | Potomac River Sailing Association | Al Girard | |
| 1996 | Severn Sailing Association | Matt D’Errico | |
| 1997 | Mike Schmidt | Magothy River Sailing Association | |
| 1998 | George Panayides | Hampton Yacht Club | |
| 1999 | Hampton Yacht Club | Anthony Kupersmith | |
| 2000 | Severn Sailing Association | Ward Hacket | Tred Avon Yacht Club |
| 2001 | Rock Hall Yacht Club | Alden Shattuck | Severn Sailing Association |
| 2002 | Fishing Bay Yacht Club | George Panayides | Hampton Yacht Club |
| 2003 | Hampton Yacht Club | Henry Amthor | Hampton Yacht Club |
| 2004 | Severn Sailing Association | Royce Weber | |
| 2005 | Rock Hall Yacht Club | Ryan Minth | |
| 2006 | Fishing Bay Yacht Club | Henry Amthor | Hampton Yacht Club |
| 2007 | Severn Sailing Association | Alden Shattuck | Severn Sailing Association |
| 2008 | Deep Creek Yacht Club | Ted Morgan | Severn Sailing Association |
| 2009 | West River Sailing Club | Eric Reitinger | Brant Beach Yacht Club |
| 2010 | Corsica River Yacht Club | Scott Houck | Annapolis Yacht Club |
| 2011 | Fishing Bay Yacht Club | John MacCausland | Cooper River Yacht Club |
| 2012 | Severn Sailing Association | Brady White | Severn Sailing Association |
| 2013 | Severn Sailing Association | Mike Russom | Greater Wildwood Yacht Club |
| 2014 | Tred Avon Yacht Club | Luke Shingledecker | Severn Sailing Association |
| 2015 | Severn Sailing Association | Luke Shingledecker | Severn Sailing Association |
| 2016 | Severn Sailing Association | Leo Boucher | Severn Sailing Association |
| 2017 | Severn Sailing Association | Leo Boucher | Severn Sailing Association |
| 2018 | Severn Sailing Association | David Grace | Severn Sailing Association |
| 2019 | Severn Sailing Association | Eric Reitinger | Brant Beach Yacht Club |
| 2020 | Severn Sailing Association | JC Hermus | USNA |
| 2021 | Norfolk Yacht & Country Club | Alex Jacob | Norfolk Yacht & Country Club |
*Prior to 2004 the District championship was awarded to the top District 11 finisher at the District Championship Regatta.
**1997 & 1998 the District Championship was awarded to the winner of the District Series of events
ILCA-NA District 11 